1H-吲哚,3-(甲硫基)-1-(苯基甲基)- | 139461-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1H-吲哚,3-(甲硫基)-1-(苯基甲基)-
• 英文名称: 1-benzyl-3-(methylthio)indole
• 英文别名: 1-benzyl-3-(methylthio)-1H-indole；1-Benzyl-3-methylsulfanylindole
• CAS: 139461-61-3
• 化学式: C₁₆H₁₅NS
• 分子量: 253.368
• InChiKey: BFKDRBILPCHLHO-UHFFFAOYSA-N

物化性质

• 沸点：
  441.4±28.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1H-吲哚,3-(甲硫基)-1-(苯基甲基)- 在 PPA 作用下， 反应 2.5h， 以82%的产率得到1-苄基-2-(甲硫基)吲哚
  参考文献：
  名称：

  Acid-catalyzed isomerization of 3-indolyl sulfides to 2-indolyl sulfides: first synthesis of 3-unsubstituted 2-arylthioindoles. Evidence for a complex intermolecular process

  摘要：

  The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the first synthesis of 3-unsubstituted 2-(arylthio)indoles, a hitherto unattainable class of compounds. When catalyzed by trifluoroacetic acid, the isomerization proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2,3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction of these species to yield the rearranged isomer 4. A mechanism is proposed involving a role for the acid in the sulfenyl-transfer steps. This type of process also occurs, to a lesser extent, in the polyphosphoric acid catalyzed isomerization.

  DOI：

  10.1021/jo00035a029
• 作为产物：
  描述：

  1-苄基吲哚 、 N-(乙基硫代)邻苯二甲酰亚胺 在 magnesium bromide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以93%的产率得到1H-吲哚,3-(甲硫基)-1-(苯基甲基)-
  参考文献：
  名称：

  铑催化下吲哚的硫醚导向的选择性C4 C–H链烯基化

  摘要：

  据报道通过五元金属环中间体形成硫醚导向的Rh（III）催化的吲哚的C4选择性C–H链烯基化。该协议允许广泛的官能团兼容性和广泛的底物范围。在C–H官能化事件发生后，可以很容易地将导向基团除去或转化成其他官能团。该催化方法也适用于涉及苯并[ b ]噻吩和苯并[ b ]呋喃骨架的相关杂环体系。

  DOI：

  10.1021/acs.orglett.8b02038

文献信息

• Methylthiolation for Electron‐Rich Heteroarenes with DMSO‐TsCl
  作者：Lei‐Yang Zhang、Yue‐Hua Wu、Nai‐Xing Wang、Xue‐Wang Gao、Zhan Yan、Bao‐Cai Xu、Ning Liu、Bo‐Zhou Wang、Yalan Xing

  DOI：10.1002/ejoc.202100001

  日期：2021.3.5

  DMSO‐TsCl is developed for methylthiolation of various heteroarenes including pyrroles, furans, thiophenes and indoles under facile conditions. This protocol features scalable, general applicability of substrates and moderate to excellent yields. An acceptable mechanism is proposed, two of the key intermediates of proposed mechanism are detected by HRMS. Further applications of this method were also

  DMSO-TsCl是为在方便条件下将各种杂芳烃进行甲基硫醇化而开发的，包括吡咯，呋喃，噻吩和吲哚。该协议具有可扩展的基板通用性，并且具有中等至极好的产量。提出了一种可以接受的机制，该机制的两个关键中间体均通过HRMS进行检测。还对该方法进行了进一步的应用。
• Iridium‐Catalyzed Direct C4‐ and C7‐Selective Alkynylation of Indoles Using Sulfur‐Directing Groups
  作者：Chandrababu Naidu Kona、Yuji Nishii、Masahiro Miura

  DOI：10.1002/anie.201904709

  日期：2019.7.15

  past century, and extensive studies have been conducted to establish practical synthetic methods for their derivatives. In particular, selective functionalization of the poorly reactive benzenoid core over the pyrrole ring has been a great challenge. Reported herein is an iridium‐catalyzed direct alkynylation of the indole C4‐ and C7‐positions with the assistance of sulfur directing groups. This transformation

  在过去的一个世纪中，吲哚及其类似物一直是最普遍的杂环之一，并且进行了广泛的研究以建立其衍生物的实用合成方法。尤其是，在吡咯环上反应性差的苯类核心的选择性官能化一直是一个巨大的挑战。本文报道的是在硫引导基团的帮助下，铱催化的C4-和C7-位吲哚基的直接炔基化。这种转变显示了广泛的功能组耐受性以及出色的位点选择性。导向基团可以容易地除去或在催化后被转化。炔烃片段的合成效用通过天然吲哚生物碱的核心结构衍生化来证明。
• Thioether-Directed C4-Selective C–H Acylmethylation of Indoles Using α-Carbonyl Sulfoxonium Ylides
  作者：Chandrababu Naidu Kona、Yuji Nishii、Masahiro Miura

  DOI：10.1021/acs.orglett.0c01617

  日期：2020.6.19

  Site-selective direct functionalization of an indole benzenoid core has been a great challenge due to its inherently poor reactivity. We herein demonstrate an iridium-catalyzed C4-selective acylmethylation of indoles using alpha-carbonyl sulfoxonium ylides as carbene precursors. This method exhibits high efficiency and broad functional group compatibility. The directing group was easily removed or converted to other functionalities after the catalysis. The potential synthetic utility of the coupling products was highlighted by constructing medium-sized polycyclic indoles.